3-Phenoxybenzyl alcohol

colourless liquidChEBI: A member of the class of benzyl alcohols that is benzyl alcohol bearing a phenoxy substituent at C-3. It is a metbaolite of the insecticide permethrin.

(3-phenoxyphenyl)methanol is a member of the class of benzyl alcohols that is benzyl alcohol bearing a phenoxy substituent at C-3. It is a metbaolite of the insecticide permethrin. It has a role as a marine xenobiotic metabolite. It is a member of benzyl alcohols and an aromatic ether.

3-phenoxy-benzaldehyde (5 g, 25.22 mmol) was dissolved in dry methanol (60 mL), cooled to 0°C, and sodium borohydride (1.14 g, 30.26 mmol) was added portionwise. The reaction mixture was stirred at room temperature for 1.5 h and then concentrated under reduced pressure. The resulting residue was treated with saturated ammonium chloride solution, extracted with ethyl acetate, dried over anhydrous sodium sulphate, and concentrated under reduced pressure to provide the desired product (99percent, 5 g). LCMS: 183.0 (M+H), Rt. 5.4 min, 93.1percent (max).General procedure: A mixture of 1a (196 mg, 1 mmol) and 1percentPd/Ni bimetallic catalyst9 (60 mg, 30 wt percent) in MeOH (10 mL) was stirred underH2 at room temperature and atmospheric pressure (on an atmosphericpressure hydrogenation apparatus) until the absorption of hydrogen ceased(3.5 h). After the catalyst was removed off by a magnetic stirring bar, thesolution was evaporated in a vaporator to give the product 2aTo a clean and dry round bottom flask SOOmL of methanol, lOOg of 3-phenoxybenzaldehyde (2)were charged and stirred for 15-20 minutes at 25-30°C. The mixture was cooled to 5-15°C and then 19.08 g of sodium borohydride was added lot wise over a period of 2-3hrs at 5-15°C. The reaction mass was stirred for 1-2hrs at 10-15°C. After completion of the reaction, the solvent is distilled off completely under vacuum and 200 mL of water was charged, then the reaction mass was stirred for 45-60 minutes at 25-30°C. The product is extracted with 3 x lOOmL oftoluene and the toluene solvent was distilled completely under vacuum. The obtained crude oil was degassed under vacuum at 65-75°C. Yield: 94percent.General procedure: To a stirred suspension of appropriate aryl halide(2.0 mmol) and phenol (2.0 mmol) in 6 ml water, Ni-alumina (0.125g, 6 mol percent ofnickel metal) was added followed by KEXAMPLE 4 EXAMPLE 5 EXAMPLE 6 Step 2:The crude product (1.02 g, 4.47 mmol) obtained in the previous step was dissolved in 15 ml of THF, NaBH4 (0.31 g, 8.0 mmol) was added in portions, Add finished, heated under reflux dropping 0.5ml methanol, Drip continued to return about 30min, The mixture was stirred and cooled to room temperature. The reaction solution was poured into 40 ml of ice water and extracted with ethyl acetate (40 ml x 3). The combined organic phases were washed with saturated brine, 50 ml x 2, dried over anhydrous sodium sulfate, The solvent was evaporated to give 0.80 g of a white solid in 80percent yield.

Molecular Weight:200.23
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:200.083729621
Monoisotopic Mass:200.083729621
Topological Polar Surface Area:29.5
Heavy Atom Count:15
Complexity:175
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes